Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes

Masaki Shimizu, Masahiro Higashi, Youhei Takeda, Guofang Jiang, Masahito Murai, Tamejiro Hiyama

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A novel method for the generation of 3,3,3-trifluoropropynyllithium is reported, which involves treatment of trifluoromethyl-substituted enol tosylate, prepared from 1,1-dichloro-3,3,3-trifluoroacetone, with two equivalents of butyllithium. Palladium-catalyzed coupling reaction of sulfonates of the carbonyl adducts with organozinc reagents gave trifluoromethyl-containing tri- and tetrasubstituted allenes.

Original languageEnglish
Pages (from-to)1163-1165
Number of pages3
JournalSynlett
Issue number7
DOIs
Publication statusPublished - Apr 24 2007
Externally publishedYes

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Palladium
propadiene
butyllithium

Keywords

  • Alkynes
  • Allenes
  • Fluorine
  • Lithium
  • Palladium

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes. / Shimizu, Masaki; Higashi, Masahiro; Takeda, Youhei; Jiang, Guofang; Murai, Masahito; Hiyama, Tamejiro.

In: Synlett, No. 7, 24.04.2007, p. 1163-1165.

Research output: Contribution to journalArticle

Shimizu, Masaki ; Higashi, Masahiro ; Takeda, Youhei ; Jiang, Guofang ; Murai, Masahito ; Hiyama, Tamejiro. / Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes. In: Synlett. 2007 ; No. 7. pp. 1163-1165.
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